Uridine monophosphate

Identification

Generic Name
Uridine monophosphate
DrugBank Accession Number
DB03685
Background

5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 324.1813
Monoisotopic: 324.035866536
Chemical Formula
C9H13N2O9P
Synonyms
  • 5'-uridylic acid
  • UMP
  • Uridine 5'-monophosphate
  • Uridine 5'-phosphoric acid
  • Uridine phosphate
  • Uridine-5'-monophosphate

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUridine-cytidine kinase-like 1Not AvailableHumans
UGalactose-1-phosphate uridylyltransferaseNot AvailableEscherichia coli (strain K12)
UThymidylate synthaseNot AvailableLactobacillus casei
UGlycosyltransferase 6 domain-containing protein 1Not AvailableHumans
UU6 snRNA-associated Sm-like protein LSm6Not AvailableHumans
UUracil phosphoribosyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UBeta-1,4-galactosyltransferase 1Not AvailableHumans
UInterferon-stimulated gene 20 kDa proteinNot AvailableHumans
UOrotidine 5'-phosphate decarboxylaseNot AvailableBacillus subtilis (strain 168)
UBifunctional protein PyrRNot AvailableBacillus caldolyticus
UUracil phosphoribosyltransferaseNot AvailableGeobacillus kaustophilus (strain HTA426)
UBifunctional polymyxin resistance protein ArnANot AvailableEscherichia coli (strain K12)
URibosomal small subunit pseudouridine synthase ANot AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Clarithromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Lactose SynthesisMetabolic
Arbekacin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
Azithromycin Action PathwayDrug action
Clindamycin Action PathwayDrug action
Erythromycin Action PathwayDrug action
Kanamycin Action PathwayDrug action
Neomycin Action PathwayDrug action
Netilmicin Action PathwayDrug action
Streptomycin Action PathwayDrug action
Clomocycline Action PathwayDrug action
Congenital Disorder of Glycosylation CDG-IIdDisease
Tobramycin Action PathwayDrug action
Rolitetracycline Action PathwayDrug action
beta-Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Telithromycin Action PathwayDrug action
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Doxycycline Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas
show 9 more
Substituents
1,2-diol / Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine ribonucleoside 5'-monophosphate, uridine 5'-phosphate (CHEBI:16695) / Ribonucleotides (C00105)
Affected organisms
Not Available

Chemical Identifiers

UNII
E2OU15WN0N
CAS number
58-97-9
InChI Key
DJJCXFVJDGTHFX-XVFCMESISA-N
InChI
InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O

References

General References
Not Available
Human Metabolome Database
HMDB0000288
KEGG Compound
C00105
PubChem Compound
6030
PubChem Substance
46506409
ChemSpider
5808
BindingDB
50398699
ChEBI
16695
ChEMBL
CHEMBL214393
ZINC
ZINC000002123545
PDBe Ligand
U
Wikipedia
Uridine_monophosphate
PDB Entries
1dbt / 1fgx / 1g8o / 1hxp / 1hxq / 1i5e / 1me0 / 1me1 / 1o5o / 1ucd
show 100 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)202 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility12.0 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.5Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.23Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area165.86 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity63.44 m3·mol-1Chemaxon
Polarizability26.3 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9132
Blood Brain Barrier+0.8209
Caco-2 permeable-0.8159
P-glycoprotein substrateNon-substrate0.7686
P-glycoprotein inhibitor INon-inhibitor0.8844
P-glycoprotein inhibitor IINon-inhibitor0.9719
Renal organic cation transporterNon-inhibitor0.9445
CYP450 2C9 substrateNon-substrate0.6802
CYP450 2D6 substrateNon-substrate0.8553
CYP450 3A4 substrateNon-substrate0.5695
CYP450 1A2 substrateNon-inhibitor0.9039
CYP450 2C9 inhibitorNon-inhibitor0.9086
CYP450 2D6 inhibitorNon-inhibitor0.91
CYP450 2C19 inhibitorNon-inhibitor0.887
CYP450 3A4 inhibitorNon-inhibitor0.9167
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.959
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9005
BiodegradationReady biodegradable0.5346
Rat acute toxicity2.0585 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9698
hERG inhibition (predictor II)Non-inhibitor0.8041
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-014i-2953000000-f54596d9a11bbe82adc5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002b-9611000000-d241a590ba092a9137ca
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-2953000000-f54596d9a11bbe82adc5
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-03fr-0194000000-c8bedd9fabaccee15ef6
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-03di-0910000000-da7fb1ddd74c36aec368
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-03di-0900000000-b2c9787a3d982ecb858e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-00ba-9102000000-f8b96709e62e0857c40a
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00ba-9102000000-f8b96709e62e0857c40a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-1952000000-e2bfdd7c0c2b89ebadf7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9004000000-9d6ea49b55d3ff3e4f62
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0910000000-e8abb7f1833217927b48
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9010000000-590002233c5c4685a44e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-c50af34854964413d9de
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-6eff6be70b8466761159
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.8786743
predicted
DarkChem Lite v0.1.0
[M-H]-180.5219743
predicted
DarkChem Lite v0.1.0
[M-H]-183.5269743
predicted
DarkChem Lite v0.1.0
[M-H]-164.56844
predicted
DeepCCS 1.0 (2019)
[M+H]+182.9251743
predicted
DarkChem Lite v0.1.0
[M+H]+182.6904743
predicted
DarkChem Lite v0.1.0
[M+H]+183.1449743
predicted
DarkChem Lite v0.1.0
[M+H]+166.92644
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.4517743
predicted
DarkChem Lite v0.1.0
[M+Na]+180.7507743
predicted
DarkChem Lite v0.1.0
[M+Na]+183.3209743
predicted
DarkChem Lite v0.1.0
[M+Na]+173.45004
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uridine kinase activity
Specific Function
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name
UCKL1
Uniprot ID
Q9NWZ5
Uniprot Name
Uridine-cytidine kinase-like 1
Molecular Weight
61140.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
galT
Uniprot ID
P09148
Uniprot Name
Galactose-1-phosphate uridylyltransferase
Molecular Weight
39645.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Lactobacillus casei
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis.
Gene Name
thyA
Uniprot ID
P00469
Uniprot Name
Thymidylate synthase
Molecular Weight
36579.235 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transferase activity, transferring hexosyl groups
Specific Function
Not Available
Gene Name
GLT6D1
Uniprot ID
Q7Z4J2
Uniprot Name
Glycosyltransferase 6 domain-containing protein 1
Molecular Weight
36273.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Component of LSm protein complexes, which are involved in RNA processing and may function in a chaperone-like manner, facilitating the efficient association of RNA processing factors with their sub...
Gene Name
LSM6
Uniprot ID
P62312
Uniprot Name
U6 snRNA-associated Sm-like protein LSm6
Molecular Weight
9127.525 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Catalyzes the conversion of uracil and 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) to UMP and diphosphate.
Gene Name
upp
Uniprot ID
Q9WZI0
Uniprot Name
Uracil phosphoribosyltransferase
Molecular Weight
23320.02 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Udp-galactosyltransferase activity
Specific Function
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoprot...
Gene Name
B4GALT1
Uniprot ID
P15291
Uniprot Name
Beta-1,4-galactosyltransferase 1
Molecular Weight
43919.895 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
U3 snorna binding
Specific Function
Interferon-induced antiviral exoribonuclease that acts on single-stranded RNA and also has minor activity towards single-stranded DNA. Exhibits antiviral activity against RNA viruses including hepa...
Gene Name
ISG20
Uniprot ID
Q96AZ6
Uniprot Name
Interferon-stimulated gene 20 kDa protein
Molecular Weight
20363.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Orotidine-5'-phosphate decarboxylase activity
Specific Function
Catalyzes the decarboxylation of orotidine 5'-monophosphate (OMP) to uridine 5'-monophosphate (UMP).
Gene Name
pyrF
Uniprot ID
P25971
Uniprot Name
Orotidine 5'-phosphate decarboxylase
Molecular Weight
25991.84 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Bacillus caldolyticus
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Regulates transcriptional attenuation of the pyrimidine nucleotide (pyr) operon by binding in a uridine-dependent manner to specific sites on pyr mRNA. This disrupts an antiterminator hairpin in th...
Gene Name
pyrR
Uniprot ID
P41007
Uniprot Name
Bifunctional protein PyrR
Molecular Weight
19937.85 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Geobacillus kaustophilus (strain HTA426)
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Catalyzes the conversion of uracil and 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) to UMP and diphosphate.
Gene Name
upp
Uniprot ID
Q5KUI3
Uniprot Name
Uracil phosphoribosyltransferase
Molecular Weight
22831.48 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-glucuronate decarboxylase activity
Specific Function
Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto-arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4-amino-4-deoxy-L-a...
Gene Name
arnA
Uniprot ID
P77398
Uniprot Name
Bifunctional polymyxin resistance protein ArnA
Molecular Weight
74288.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Rna binding
Specific Function
Responsible for synthesis of pseudouridine from uracil-516 in 16S ribosomal RNA.
Gene Name
rsuA
Uniprot ID
P0AA43
Uniprot Name
Ribosomal small subunit pseudouridine synthase A
Molecular Weight
25865.12 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52